This invention relates to N'-substituted-N,N'-diacylhydrazines which are useful as insecticides, compositions containing those compounds and methods of their use. This invention also relates to the production of intermediates useful in the production of such compounds.
The search for compounds which have a combination of excellent insecticidal activity and low undesirable toxicity is a continuing one because of factors such as the desire for compounds exhibiting greater activity, better selectivity, lower undesirable environmental impact, lower production and market cost and higher effectiveness against insects which are or become resistant to many known insecticides.
Prior processes for the production of the 3-alkoxy-2-alkylbenzoic acid intermediates, useful in the production of some of the N'-substituted-N,N'-diacylhydrazines of the present invention have the production of 3-hydroxy-2-alkylbenzoic acid compounds from hydrochloride salt of 2-alkyl-3-aminobenzoic acid as a preceding step. Such exothermic anilinium hydrochloride salt reactions pose reaction safety and substance stability concerns and require controlled cooling. Such constraints can create safety and cost burdens on the production of the useful intermediates concerned herein.
Furthermore, prior processes for the production of 2-alkyl-3,4-alkylenedioxybenzoic acid intermediates useful in the production of some of the other N'-substituted-N,N'-diacylhydrazines of the present invention involve the use of activating/protecting groups in place of the carboxy group and require extra steps for conversion to the benzoic acid.
There continues to be a need to develop insecticidal compounds having improved insecticidal and methods of production properties as described above. There also continues to be a need to develop safened processes for the production of the intermediate compounds useful in such methods. The present invention provides improved N'-substituted-N,N'-diacylhydrazines which are unexpectedly propertied with enhanced, higher activity as well as a safened method for production of intermediates useful for their production. The combination of higher activity, better economics of manufacture, and safer production methods can provide an economic and environmental advantage in the use of the inventive compounds.